Files
nanobot/tests/channels/test_email_channel.py
T

1870 lines
61 KiB
Python

import imaplib
from datetime import date
from email.message import EmailMessage
from pathlib import Path
import pytest
from nanobot.bus.events import OutboundMessage
from nanobot.bus.outbound_events import ProgressEvent
from nanobot.bus.queue import MessageBus
from nanobot.channels.email import EmailChannel, EmailConfig
def _make_config(**overrides) -> EmailConfig:
defaults = dict(
enabled=True,
consent_granted=True,
imap_host="imap.example.com",
imap_port=993,
imap_username="bot@example.com",
imap_password="secret",
smtp_host="smtp.example.com",
smtp_port=587,
smtp_username="bot@example.com",
smtp_password="secret",
mark_seen=True,
allow_from=["*"],
# Disable auth verification by default so existing tests are unaffected
verify_dkim=False,
verify_spf=False,
)
defaults.update(overrides)
return EmailConfig(**defaults)
def _make_raw_email(
from_addr: str = "alice@example.com",
subject: str = "Hello",
body: str = "This is the body.",
auth_results: str | None = None,
) -> bytes:
msg = EmailMessage()
msg["From"] = from_addr
msg["To"] = "bot@example.com"
msg["Subject"] = subject
msg["Message-ID"] = "<m1@example.com>"
if auth_results:
msg["Authentication-Results"] = auth_results
msg.set_content(body)
return msg.as_bytes()
def test_fetch_new_messages_parses_unseen_and_marks_seen(monkeypatch) -> None:
raw = _make_raw_email(subject="Invoice", body="Please pay")
class FakeIMAP:
def __init__(self) -> None:
self.store_calls: list[tuple[bytes, str, str]] = []
def login(self, _user: str, _pw: str):
return "OK", [b"logged in"]
def select(self, _mailbox: str):
return "OK", [b"1"]
def search(self, *_args):
return "OK", [b"1"]
def fetch(self, _imap_id: bytes, _parts: str):
return "OK", [(b"1 (UID 123 BODY[] {200})", raw), b")"]
def store(self, imap_id: bytes, op: str, flags: str):
self.store_calls.append((imap_id, op, flags))
return "OK", [b""]
def logout(self):
return "BYE", [b""]
fake = FakeIMAP()
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
channel = EmailChannel(_make_config(), MessageBus())
items, skipped_uids = channel._fetch_new_messages()
assert len(items) == 1
assert items[0]["sender"] == "alice@example.com"
assert items[0]["subject"] == "Invoice"
assert "Please pay" in items[0]["content"]
assert fake.store_calls == [(b"1", "+FLAGS", "\\Seen")]
assert skipped_uids == set()
# Same UID should be deduped in-process.
items_again, skipped_again = channel._fetch_new_messages()
assert items_again == []
assert skipped_again == set()
def test_fetch_new_messages_returns_accepted_and_skipped_uids(monkeypatch) -> None:
raw = _make_raw_email(subject="Invoice", body="Please pay")
class FakeIMAP:
def login(self, _user: str, _pw: str):
return "OK", [b"logged in"]
def select(self, _mailbox: str):
return "OK", [b"1"]
def search(self, *_args):
return "OK", [b"1"]
def fetch(self, _imap_id: bytes, _parts: str):
return "OK", [(b"1 (UID 123 BODY[] {200})", raw), b")"]
def store(self, _imap_id: bytes, _op: str, _flags: str):
return "OK", [b""]
def logout(self):
return "BYE", [b""]
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: FakeIMAP())
channel = EmailChannel(_make_config(post_action="delete"), MessageBus())
items, skipped_uids = channel._fetch_new_messages()
assert len(items) == 1
assert items[0]["metadata"]["uid"] == "123"
assert skipped_uids == set()
def test_fetch_new_messages_rejected_returns_skipped_uid(monkeypatch) -> None:
raw = _make_raw_email(from_addr="Nanobot <bot@example.com>", subject="Loop test")
class FakeIMAP:
def login(self, _user: str, _pw: str):
return "OK", [b"logged in"]
def select(self, _mailbox: str):
return "OK", [b"1"]
def search(self, *_args):
return "OK", [b"1"]
def fetch(self, _imap_id: bytes, _parts: str):
return "OK", [(b"1 (UID 123 BODY[] {200})", raw), b")"]
def store(self, _imap_id: bytes, _op: str, _flags: str):
return "OK", [b""]
def logout(self):
return "BYE", [b""]
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: FakeIMAP())
channel_skip = EmailChannel(
_make_config(from_address="bot@example.com", post_action="delete", post_action_ignore_skipped=True),
MessageBus(),
)
assert channel_skip._fetch_new_messages() == ([], {"123"})
channel_apply = EmailChannel(
_make_config(from_address="bot@example.com", post_action="delete", post_action_ignore_skipped=False),
MessageBus(),
)
items, skipped_uids = channel_apply._fetch_new_messages()
assert items == []
assert skipped_uids == {"123"}
def test_apply_post_actions_batch_delete_uses_one_connection(monkeypatch) -> None:
raw = _make_raw_email(subject="Invoice", body="Please pay")
class FakeIMAP:
def __init__(self) -> None:
self.search_calls: list[tuple] = []
self.uid_calls: list[tuple] = []
self.store_calls: list[tuple[bytes, str, str]] = []
self.expunge_calls = 0
def login(self, _user: str, _pw: str):
return "OK", [b"logged in"]
def select(self, _mailbox: str):
return "OK", [b"1"]
def search(self, *_args):
self.search_calls.append(_args)
if len(_args) >= 3 and _args[1] == "UID":
return "OK", [b"1"]
return "OK", [b"1"]
def capability(self):
return "OK", [b"IMAP4rev1 UIDPLUS"]
def uid(self, command: str, *args):
self.uid_calls.append((command, *args))
if command == "STORE":
return "OK", [b""]
if command == "EXPUNGE":
return "OK", [b""]
return "BAD", [b""]
def fetch(self, _imap_id: bytes, _parts: str):
return "OK", [(b"1 (UID 123 BODY[] {200})", raw), b")"]
def store(self, imap_id: bytes, op: str, flags: str):
self.store_calls.append((imap_id, op, flags))
return "OK", [b""]
def expunge(self):
self.expunge_calls += 1
return "OK", [b""]
def logout(self):
return "BYE", [b""]
fake = FakeIMAP()
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
channel = EmailChannel(_make_config(post_action="delete"), MessageBus())
channel._apply_post_actions_batch(["123", "124"])
assert fake.store_calls == []
assert fake.expunge_calls == 0
assert fake.search_calls == []
assert fake.uid_calls == [
("STORE", "123", "+FLAGS", "(\\Deleted)"),
("EXPUNGE", "123"),
("STORE", "124", "+FLAGS", "(\\Deleted)"),
("EXPUNGE", "124"),
]
def test_apply_post_actions_batch_move_copies_then_deletes(monkeypatch) -> None:
class FakeIMAP:
def __init__(self) -> None:
self.uid_calls: list[tuple] = []
self.store_calls: list[tuple[bytes, str, str]] = []
self.expunge_calls = 0
def login(self, _user: str, _pw: str):
return "OK", [b"logged in"]
def select(self, _mailbox: str):
return "OK", [b"1"]
def search(self, *_args):
return "OK", [b"1"]
def capability(self):
return "OK", [b"IMAP4rev1 UIDPLUS"]
def uid(self, command: str, *args):
self.uid_calls.append((command, *args))
if command == "COPY":
return "OK", [b""]
if command == "STORE":
return "OK", [b""]
if command == "EXPUNGE":
return "OK", [b""]
return "BAD", [b""]
def store(self, imap_id: bytes, op: str, flags: str):
self.store_calls.append((imap_id, op, flags))
return "OK", [b""]
def expunge(self):
self.expunge_calls += 1
return "OK", [b""]
def logout(self):
return "BYE", [b""]
fake = FakeIMAP()
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
channel = EmailChannel(
_make_config(post_action="move", post_action_move_mailbox="Processed"),
MessageBus(),
)
channel._apply_post_actions_batch(["123"])
assert fake.uid_calls == [
("COPY", "123", "Processed"),
("STORE", "123", "+FLAGS", "(\\Deleted)"),
("EXPUNGE", "123"),
]
assert fake.store_calls == []
assert fake.expunge_calls == 0
def test_apply_post_actions_batch_move_prefers_uid_move_when_supported(monkeypatch) -> None:
class FakeIMAP:
def __init__(self) -> None:
self.uid_calls: list[tuple] = []
def login(self, _user: str, _pw: str):
return "OK", [b"logged in"]
def select(self, _mailbox: str):
return "OK", [b"1"]
def capability(self):
return "OK", [b"IMAP4rev1 UIDPLUS MOVE"]
def uid(self, command: str, *args):
self.uid_calls.append((command, *args))
if command == "MOVE":
return "OK", [b""]
return "BAD", [b""]
def logout(self):
return "BYE", [b""]
fake = FakeIMAP()
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
channel = EmailChannel(
_make_config(post_action="move", post_action_move_mailbox="Processed"),
MessageBus(),
)
channel._apply_post_actions_batch(["123"])
assert fake.uid_calls == [("MOVE", "123", "Processed")]
def test_apply_post_actions_batch_fallback_caches_uid_store_failure(monkeypatch) -> None:
class FakeIMAP:
def __init__(self) -> None:
self.uid_calls: list[tuple] = []
self.search_calls: list[tuple] = []
self.store_calls: list[tuple[bytes, str, str]] = []
self.expunge_calls = 0
def login(self, _user: str, _pw: str):
return "OK", [b"logged in"]
def select(self, _mailbox: str):
return "OK", [b"2"]
def capability(self):
return "OK", [b"IMAP4rev1"]
def uid(self, command: str, *args):
self.uid_calls.append((command, *args))
if command == "STORE":
return "NO", [b"unsupported"]
return "BAD", [b""]
def search(self, *_args):
self.search_calls.append(_args)
if _args == (None, "UID", "123"):
return "OK", [b"1"]
if _args == (None, "UID", "124"):
return "OK", [b"2"]
return "NO", [b""]
def store(self, imap_id: bytes, op: str, flags: str):
self.store_calls.append((imap_id, op, flags))
return "OK", [b""]
def expunge(self):
self.expunge_calls += 1
return "OK", [b""]
def logout(self):
return "BYE", [b""]
fake = FakeIMAP()
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
channel = EmailChannel(_make_config(post_action="delete"), MessageBus())
channel._apply_post_actions_batch(["123", "124"])
# UID STORE should be attempted only once, then cached as unsupported.
assert [call for call in fake.uid_calls if call[0] == "STORE"] == [("STORE", "123", "+FLAGS", "(\\Deleted)")]
assert fake.search_calls == [(None, "UID", "123"), (None, "UID", "124")]
assert fake.store_calls == [(b"1", "+FLAGS", "\\Deleted"), (b"2", "+FLAGS", "\\Deleted")]
# With post_action_expunge=False (default), no broad expunge is called
assert fake.expunge_calls == 0
def test_apply_post_actions_batch_delete_with_post_action_expunge_true_no_uidplus(monkeypatch) -> None:
"""When post_action_expunge=True and UIDPLUS is unsupported, broad expunge IS called."""
class FakeIMAP:
def __init__(self) -> None:
self.uid_calls: list[tuple] = []
self.store_calls: list[tuple[bytes, str, str]] = []
self.expunge_calls = 0
def login(self, _user: str, _pw: str):
return "OK", [b"logged in"]
def select(self, _mailbox: str):
return "OK", [b"2"]
def capability(self):
return "OK", [b"IMAP4rev1"]
def uid(self, command: str, *args):
self.uid_calls.append((command, *args))
if command == "STORE":
return "NO", [b"unsupported"]
return "BAD", [b""]
def search(self, *_args):
uid_to_seq = {"123": b"1", "124": b"2"}
uid = _args[-1]
seq = uid_to_seq.get(uid, b"")
return "OK", [seq]
def store(self, imap_id: bytes, op: str, flags: str):
self.store_calls.append((imap_id, op, flags))
return "OK", [b""]
def expunge(self):
self.expunge_calls += 1
return "OK", [b""]
def logout(self):
return "BYE", [b""]
fake = FakeIMAP()
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
channel = EmailChannel(_make_config(post_action="delete", post_action_expunge=True), MessageBus())
channel._apply_post_actions_batch(["123", "124"])
assert fake.store_calls == [(b"1", "+FLAGS", "\\Deleted"), (b"2", "+FLAGS", "\\Deleted")]
# Broad expunge called because post_action_expunge=True
assert fake.expunge_calls == 2
@pytest.mark.asyncio
async def test_start_applies_post_action_only_after_delivery(monkeypatch) -> None:
calls: list[str] = []
channel = EmailChannel(_make_config(post_action="delete"), MessageBus())
fetched = ([
{
"sender": "alice@example.com",
"subject": "Hi",
"message_id": "<m1@example.com>",
"content": "hello",
"metadata": {"uid": "123"},
}
], [])
def _fake_fetch():
channel._running = False
return fetched
async def _fake_handle_message(**_kwargs):
calls.append("delivered")
def _fake_batch(actions):
assert calls == ["delivered"]
assert actions == ["123"]
calls.append("post_action")
monkeypatch.setattr(channel, "_fetch_new_messages", _fake_fetch)
monkeypatch.setattr(channel, "_handle_message", _fake_handle_message)
monkeypatch.setattr(channel, "_apply_post_actions_batch", _fake_batch)
await channel.start()
assert calls == ["delivered", "post_action"]
@pytest.mark.asyncio
async def test_start_skips_post_action_when_delivery_fails(monkeypatch) -> None:
called = {"post_action": False}
channel = EmailChannel(_make_config(post_action="delete"), MessageBus())
fetched = ([
{
"sender": "alice@example.com",
"subject": "Hi",
"message_id": "<m1@example.com>",
"content": "hello",
"metadata": {"uid": "123"},
}
], [])
def _fake_fetch():
channel._running = False
return fetched
async def _fake_handle_message(**_kwargs):
raise RuntimeError("delivery failed")
def _fake_batch(_actions):
called["post_action"] = True
monkeypatch.setattr(channel, "_fetch_new_messages", _fake_fetch)
monkeypatch.setattr(channel, "_handle_message", _fake_handle_message)
monkeypatch.setattr(channel, "_apply_post_actions_batch", _fake_batch)
await channel.start()
assert called["post_action"] is False
@pytest.mark.asyncio
async def test_start_keeps_post_actions_for_successful_emails_when_later_delivery_fails(monkeypatch) -> None:
called_actions: list[str] = []
channel = EmailChannel(_make_config(post_action="delete"), MessageBus())
fetched = ([
{
"sender": "alice@example.com",
"subject": "First",
"message_id": "<m1@example.com>",
"content": "ok",
"metadata": {"uid": "123"},
},
{
"sender": "bob@example.com",
"subject": "Second",
"message_id": "<m2@example.com>",
"content": "fail",
"metadata": {"uid": "124"},
},
], [])
def _fake_fetch():
channel._running = False
return fetched
async def _fake_handle_message(**kwargs):
if kwargs["chat_id"] == "bob@example.com":
raise RuntimeError("delivery failed")
def _fake_batch(actions):
called_actions.extend(actions)
monkeypatch.setattr(channel, "_fetch_new_messages", _fake_fetch)
monkeypatch.setattr(channel, "_handle_message", _fake_handle_message)
monkeypatch.setattr(channel, "_apply_post_actions_batch", _fake_batch)
await channel.start()
assert called_actions == ["123"]
def test_fetch_new_messages_skips_self_sent_email_and_marks_seen(monkeypatch) -> None:
raw = _make_raw_email(from_addr="Nanobot <bot@example.com>", subject="Loop test")
class FakeIMAP:
def __init__(self) -> None:
self.store_calls: list[tuple[bytes, str, str]] = []
def login(self, _user: str, _pw: str):
return "OK", [b"logged in"]
def select(self, _mailbox: str):
return "OK", [b"1"]
def search(self, *_args):
return "OK", [b"1"]
def fetch(self, _imap_id: bytes, _parts: str):
return "OK", [(b"1 (UID 123 BODY[] {200})", raw), b")"]
def store(self, imap_id: bytes, op: str, flags: str):
self.store_calls.append((imap_id, op, flags))
return "OK", [b""]
def logout(self):
return "BYE", [b""]
fake = FakeIMAP()
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
channel = EmailChannel(_make_config(from_address="bot@example.com"), MessageBus())
items, skipped_uids = channel._fetch_new_messages()
assert items == []
assert skipped_uids == {"123"}
assert fake.store_calls == [(b"1", "+FLAGS", "\\Seen")]
# Same UID should still be deduped after being ignored.
items_again, skipped_again = channel._fetch_new_messages()
assert items_again == []
assert skipped_again == set()
@pytest.mark.parametrize(
"config_override,from_header",
[
# Only smtp_username matches — simulates an SMTP relay where
# outbound From gets rewritten to the SMTP login identity.
(
{"from_address": "", "smtp_username": "bot@example.com", "imap_username": "other@imap.com"},
"bot@example.com",
),
# Only imap_username matches — simulates mailbox-based identity
# with no explicit from_address set.
(
{"from_address": "", "smtp_username": "other@smtp.com", "imap_username": "bot@example.com"},
"bot@example.com",
),
# Case-insensitive: inbound From arrives upper-cased.
(
{"from_address": "bot@example.com", "smtp_username": "other@smtp.com", "imap_username": "other@imap.com"},
"BOT@EXAMPLE.COM",
),
],
ids=["smtp_username_only", "imap_username_only", "case_insensitive"],
)
def test_fetch_new_messages_skips_self_sent_across_identity_sources(
monkeypatch, config_override, from_header
) -> None:
"""Self-address detection must fire when any of from_address / smtp_username /
imap_username matches, and must be case-insensitive."""
raw = _make_raw_email(from_addr=from_header, subject="Loop test")
class FakeIMAP:
def __init__(self) -> None:
self.store_calls: list[tuple[bytes, str, str]] = []
def login(self, _user: str, _pw: str):
return "OK", [b"logged in"]
def select(self, _mailbox: str):
return "OK", [b"1"]
def search(self, *_args):
return "OK", [b"1"]
def fetch(self, _imap_id: bytes, _parts: str):
return "OK", [(b"1 (UID 123 BODY[] {200})", raw), b")"]
def store(self, imap_id: bytes, op: str, flags: str):
self.store_calls.append((imap_id, op, flags))
return "OK", [b""]
def logout(self):
return "BYE", [b""]
fake = FakeIMAP()
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
channel = EmailChannel(_make_config(**config_override), MessageBus())
items, _ = channel._fetch_new_messages()
assert items == []
assert fake.store_calls == [(b"1", "+FLAGS", "\\Seen")]
def test_fetch_new_messages_retries_once_when_imap_connection_goes_stale(monkeypatch) -> None:
raw = _make_raw_email(subject="Invoice", body="Please pay")
fail_once = {"pending": True}
class FlakyIMAP:
def __init__(self) -> None:
self.store_calls: list[tuple[bytes, str, str]] = []
self.search_calls = 0
def login(self, _user: str, _pw: str):
return "OK", [b"logged in"]
def select(self, _mailbox: str):
return "OK", [b"1"]
def search(self, *_args):
self.search_calls += 1
if fail_once["pending"]:
fail_once["pending"] = False
raise imaplib.IMAP4.abort("socket error")
return "OK", [b"1"]
def fetch(self, _imap_id: bytes, _parts: str):
return "OK", [(b"1 (UID 123 BODY[] {200})", raw), b")"]
def store(self, imap_id: bytes, op: str, flags: str):
self.store_calls.append((imap_id, op, flags))
return "OK", [b""]
def logout(self):
return "BYE", [b""]
fake_instances: list[FlakyIMAP] = []
def _factory(_host: str, _port: int):
instance = FlakyIMAP()
fake_instances.append(instance)
return instance
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", _factory)
channel = EmailChannel(_make_config(), MessageBus())
items, _ = channel._fetch_new_messages()
assert len(items) == 1
assert len(fake_instances) == 2
assert fake_instances[0].search_calls == 1
assert fake_instances[1].search_calls == 1
def test_fetch_new_messages_keeps_messages_collected_before_stale_retry(monkeypatch) -> None:
raw_first = _make_raw_email(subject="First", body="First body")
raw_second = _make_raw_email(subject="Second", body="Second body")
mailbox_state = {
b"1": {"uid": b"123", "raw": raw_first, "seen": False},
b"2": {"uid": b"124", "raw": raw_second, "seen": False},
}
fail_once = {"pending": True}
class FlakyIMAP:
def login(self, _user: str, _pw: str):
return "OK", [b"logged in"]
def select(self, _mailbox: str):
return "OK", [b"2"]
def search(self, *_args):
unseen_ids = [imap_id for imap_id, item in mailbox_state.items() if not item["seen"]]
return "OK", [b" ".join(unseen_ids)]
def fetch(self, imap_id: bytes, _parts: str):
if imap_id == b"2" and fail_once["pending"]:
fail_once["pending"] = False
raise imaplib.IMAP4.abort("socket error")
item = mailbox_state[imap_id]
header = b"%s (UID %s BODY[] {200})" % (imap_id, item["uid"])
return "OK", [(header, item["raw"]), b")"]
def store(self, imap_id: bytes, _op: str, _flags: str):
mailbox_state[imap_id]["seen"] = True
return "OK", [b""]
def logout(self):
return "BYE", [b""]
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: FlakyIMAP())
channel = EmailChannel(_make_config(), MessageBus())
items, _ = channel._fetch_new_messages()
assert [item["subject"] for item in items] == ["First", "Second"]
def test_fetch_new_messages_skips_missing_mailbox(monkeypatch) -> None:
class MissingMailboxIMAP:
def login(self, _user: str, _pw: str):
return "OK", [b"logged in"]
def select(self, _mailbox: str):
raise imaplib.IMAP4.error("Mailbox doesn't exist")
def logout(self):
return "BYE", [b""]
monkeypatch.setattr(
"nanobot.channels.email.imaplib.IMAP4_SSL",
lambda _h, _p: MissingMailboxIMAP(),
)
channel = EmailChannel(_make_config(), MessageBus())
assert channel._fetch_new_messages() == ([], set())
def test_validate_config_requires_move_mailbox_for_move_post_action() -> None:
channel = EmailChannel(_make_config(post_action="move", post_action_move_mailbox=None), MessageBus())
assert channel._validate_config() is False
def test_extract_text_body_falls_back_to_html() -> None:
msg = EmailMessage()
msg["From"] = "alice@example.com"
msg["To"] = "bot@example.com"
msg["Subject"] = "HTML only"
msg.add_alternative("<p>Hello<br>world</p>", subtype="html")
text = EmailChannel._extract_text_body(msg)
assert "Hello" in text
assert "world" in text
@pytest.mark.asyncio
async def test_start_returns_immediately_without_consent(monkeypatch) -> None:
cfg = _make_config()
cfg.consent_granted = False
channel = EmailChannel(cfg, MessageBus())
called = {"fetch": False}
def _fake_fetch():
called["fetch"] = True
return []
monkeypatch.setattr(channel, "_fetch_new_messages", _fake_fetch)
await channel.start()
assert channel.is_running is False
assert called["fetch"] is False
@pytest.mark.asyncio
async def test_send_uses_smtp_and_reply_subject(monkeypatch) -> None:
class FakeSMTP:
def __init__(self, _host: str, _port: int, timeout: int = 30) -> None:
self.timeout = timeout
self.started_tls = False
self.logged_in = False
self.sent_messages: list[EmailMessage] = []
def __enter__(self):
return self
def __exit__(self, exc_type, exc, tb):
return False
def starttls(self, context=None):
self.started_tls = True
def login(self, _user: str, _pw: str):
self.logged_in = True
def send_message(self, msg: EmailMessage):
self.sent_messages.append(msg)
fake_instances: list[FakeSMTP] = []
def _smtp_factory(host: str, port: int, timeout: int = 30):
instance = FakeSMTP(host, port, timeout=timeout)
fake_instances.append(instance)
return instance
monkeypatch.setattr("nanobot.channels.email.smtplib.SMTP", _smtp_factory)
channel = EmailChannel(_make_config(), MessageBus())
channel._last_subject_by_chat["alice@example.com"] = "Invoice #42"
channel._last_message_id_by_chat["alice@example.com"] = "<m1@example.com>"
await channel.send(
OutboundMessage(
channel="email",
chat_id="alice@example.com",
content="Acknowledged.",
)
)
assert len(fake_instances) == 1
smtp = fake_instances[0]
assert smtp.started_tls is True
assert smtp.logged_in is True
assert len(smtp.sent_messages) == 1
sent = smtp.sent_messages[0]
assert sent["Subject"] == "Re: Invoice #42"
assert sent["To"] == "alice@example.com"
assert sent["In-Reply-To"] == "<m1@example.com>"
@pytest.mark.asyncio
async def test_send_skips_progress_messages_before_smtp(monkeypatch) -> None:
called = {"smtp": False}
def _smtp_factory(*_args, **_kwargs):
called["smtp"] = True
raise AssertionError("progress messages must not open an SMTP connection")
monkeypatch.setattr("nanobot.channels.email.smtplib.SMTP", _smtp_factory)
channel = EmailChannel(_make_config(), MessageBus())
await channel.send(
OutboundMessage(
channel="email",
chat_id="alice@example.com",
content="",
event=ProgressEvent(tool_events=[{"phase": "end", "name": "exec"}]),
)
)
assert called["smtp"] is False
@pytest.mark.asyncio
async def test_send_skips_reply_when_auto_reply_disabled(monkeypatch) -> None:
"""When auto_reply_enabled=False, replies should be skipped but proactive sends allowed."""
class FakeSMTP:
def __init__(self, _host: str, _port: int, timeout: int = 30) -> None:
self.sent_messages: list[EmailMessage] = []
def __enter__(self):
return self
def __exit__(self, exc_type, exc, tb):
return False
def starttls(self, context=None):
return None
def login(self, _user: str, _pw: str):
return None
def send_message(self, msg: EmailMessage):
self.sent_messages.append(msg)
fake_instances: list[FakeSMTP] = []
def _smtp_factory(host: str, port: int, timeout: int = 30):
instance = FakeSMTP(host, port, timeout=timeout)
fake_instances.append(instance)
return instance
monkeypatch.setattr("nanobot.channels.email.smtplib.SMTP", _smtp_factory)
cfg = _make_config()
cfg.auto_reply_enabled = False
channel = EmailChannel(cfg, MessageBus())
# Mark alice as someone who sent us an email (making this a "reply")
channel._last_subject_by_chat["alice@example.com"] = "Previous email"
# Reply should be skipped (auto_reply_enabled=False)
await channel.send(
OutboundMessage(
channel="email",
chat_id="alice@example.com",
content="Should not send.",
)
)
assert fake_instances == []
# Reply with force_send=True should be sent
await channel.send(
OutboundMessage(
channel="email",
chat_id="alice@example.com",
content="Force send.",
metadata={"force_send": True},
)
)
assert len(fake_instances) == 1
assert len(fake_instances[0].sent_messages) == 1
@pytest.mark.asyncio
async def test_send_proactive_email_when_auto_reply_disabled(monkeypatch) -> None:
"""Proactive emails (not replies) should be sent even when auto_reply_enabled=False."""
class FakeSMTP:
def __init__(self, _host: str, _port: int, timeout: int = 30) -> None:
self.sent_messages: list[EmailMessage] = []
def __enter__(self):
return self
def __exit__(self, exc_type, exc, tb):
return False
def starttls(self, context=None):
return None
def login(self, _user: str, _pw: str):
return None
def send_message(self, msg: EmailMessage):
self.sent_messages.append(msg)
fake_instances: list[FakeSMTP] = []
def _smtp_factory(host: str, port: int, timeout: int = 30):
instance = FakeSMTP(host, port, timeout=timeout)
fake_instances.append(instance)
return instance
monkeypatch.setattr("nanobot.channels.email.smtplib.SMTP", _smtp_factory)
cfg = _make_config()
cfg.auto_reply_enabled = False
channel = EmailChannel(cfg, MessageBus())
# bob@example.com has never sent us an email (proactive send)
# This should be sent even with auto_reply_enabled=False
await channel.send(
OutboundMessage(
channel="email",
chat_id="bob@example.com",
content="Hello, this is a proactive email.",
)
)
assert len(fake_instances) == 1
assert len(fake_instances[0].sent_messages) == 1
sent = fake_instances[0].sent_messages[0]
assert sent["To"] == "bob@example.com"
@pytest.mark.asyncio
async def test_send_skips_when_consent_not_granted(monkeypatch) -> None:
class FakeSMTP:
def __init__(self, _host: str, _port: int, timeout: int = 30) -> None:
self.sent_messages: list[EmailMessage] = []
def __enter__(self):
return self
def __exit__(self, exc_type, exc, tb):
return False
def starttls(self, context=None):
return None
def login(self, _user: str, _pw: str):
return None
def send_message(self, msg: EmailMessage):
self.sent_messages.append(msg)
called = {"smtp": False}
def _smtp_factory(host: str, port: int, timeout: int = 30):
called["smtp"] = True
return FakeSMTP(host, port, timeout=timeout)
monkeypatch.setattr("nanobot.channels.email.smtplib.SMTP", _smtp_factory)
cfg = _make_config()
cfg.consent_granted = False
channel = EmailChannel(cfg, MessageBus())
await channel.send(
OutboundMessage(
channel="email",
chat_id="alice@example.com",
content="Should not send.",
metadata={"force_send": True},
)
)
assert called["smtp"] is False
def test_fetch_messages_between_dates_uses_imap_since_before_without_mark_seen(monkeypatch) -> None:
raw = _make_raw_email(subject="Status", body="Yesterday update")
class FakeIMAP:
def __init__(self) -> None:
self.search_args = None
self.store_calls: list[tuple[bytes, str, str]] = []
def login(self, _user: str, _pw: str):
return "OK", [b"logged in"]
def select(self, _mailbox: str):
return "OK", [b"1"]
def search(self, *_args):
self.search_args = _args
return "OK", [b"5"]
def fetch(self, _imap_id: bytes, _parts: str):
return "OK", [(b"5 (UID 999 BODY[] {200})", raw), b")"]
def store(self, imap_id: bytes, op: str, flags: str):
self.store_calls.append((imap_id, op, flags))
return "OK", [b""]
def logout(self):
return "BYE", [b""]
fake = FakeIMAP()
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
channel = EmailChannel(_make_config(), MessageBus())
items = channel.fetch_messages_between_dates(
start_date=date(2026, 2, 6),
end_date=date(2026, 2, 7),
limit=10,
)
assert len(items) == 1
assert items[0]["subject"] == "Status"
# search(None, "SINCE", "06-Feb-2026", "BEFORE", "07-Feb-2026")
assert fake.search_args is not None
assert fake.search_args[1:] == ("SINCE", "06-Feb-2026", "BEFORE", "07-Feb-2026")
assert fake.store_calls == []
# ---------------------------------------------------------------------------
# Security: Anti-spoofing tests for Authentication-Results verification
# ---------------------------------------------------------------------------
def _make_fake_imap(raw: bytes):
"""Return a FakeIMAP class pre-loaded with the given raw email."""
class FakeIMAP:
def __init__(self) -> None:
self.store_calls: list[tuple[bytes, str, str]] = []
def login(self, _user: str, _pw: str):
return "OK", [b"logged in"]
def select(self, _mailbox: str):
return "OK", [b"1"]
def search(self, *_args):
return "OK", [b"1"]
def fetch(self, _imap_id: bytes, _parts: str):
return "OK", [(b"1 (UID 500 BODY[] {200})", raw), b")"]
def store(self, imap_id: bytes, op: str, flags: str):
self.store_calls.append((imap_id, op, flags))
return "OK", [b""]
def logout(self):
return "BYE", [b""]
return FakeIMAP()
def test_spoofed_email_rejected_when_verify_enabled(monkeypatch) -> None:
"""An email without Authentication-Results should be rejected when verify_dkim=True."""
raw = _make_raw_email(subject="Spoofed", body="Malicious payload")
fake = _make_fake_imap(raw)
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
cfg = _make_config(verify_dkim=True, verify_spf=True)
channel = EmailChannel(cfg, MessageBus())
items, _ = channel._fetch_new_messages()
assert len(items) == 0, "Spoofed email without auth headers should be rejected"
def test_email_with_valid_auth_results_accepted(monkeypatch) -> None:
"""An email with spf=pass and dkim=pass should be accepted."""
raw = _make_raw_email(
subject="Legit",
body="Hello from verified sender",
auth_results="mx.example.com; spf=pass smtp.mailfrom=alice@example.com; dkim=pass header.d=example.com",
)
fake = _make_fake_imap(raw)
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
cfg = _make_config(verify_dkim=True, verify_spf=True)
channel = EmailChannel(cfg, MessageBus())
items, _ = channel._fetch_new_messages()
assert len(items) == 1
assert items[0]["sender"] == "alice@example.com"
assert items[0]["subject"] == "Legit"
def test_email_with_partial_auth_rejected(monkeypatch) -> None:
"""An email with only spf=pass but no dkim=pass should be rejected when verify_dkim=True."""
raw = _make_raw_email(
subject="Partial",
body="Only SPF passes",
auth_results="mx.example.com; spf=pass smtp.mailfrom=alice@example.com; dkim=fail",
)
fake = _make_fake_imap(raw)
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
cfg = _make_config(verify_dkim=True, verify_spf=True)
channel = EmailChannel(cfg, MessageBus())
items, _ = channel._fetch_new_messages()
assert len(items) == 0, "Email with dkim=fail should be rejected"
def test_backward_compat_verify_disabled(monkeypatch) -> None:
"""When verify_dkim=False and verify_spf=False, emails without auth headers are accepted."""
raw = _make_raw_email(subject="NoAuth", body="No auth headers present")
fake = _make_fake_imap(raw)
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
cfg = _make_config(verify_dkim=False, verify_spf=False)
channel = EmailChannel(cfg, MessageBus())
items, _ = channel._fetch_new_messages()
assert len(items) == 1, "With verification disabled, emails should be accepted as before"
def test_email_content_tagged_with_email_context(monkeypatch) -> None:
"""Email content should be prefixed with [EMAIL-CONTEXT] for LLM isolation."""
raw = _make_raw_email(subject="Tagged", body="Check the tag")
fake = _make_fake_imap(raw)
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
cfg = _make_config(verify_dkim=False, verify_spf=False)
channel = EmailChannel(cfg, MessageBus())
items, _ = channel._fetch_new_messages()
assert len(items) == 1
assert items[0]["content"].startswith("[EMAIL-CONTEXT]"), (
"Email content must be tagged with [EMAIL-CONTEXT]"
)
def test_check_authentication_results_method() -> None:
"""Unit test for the _check_authentication_results static method."""
from email import policy
from email.parser import BytesParser
# No Authentication-Results header
msg_no_auth = EmailMessage()
msg_no_auth["From"] = "alice@example.com"
msg_no_auth.set_content("test")
parsed = BytesParser(policy=policy.default).parsebytes(msg_no_auth.as_bytes())
spf, dkim = EmailChannel._check_authentication_results(parsed)
assert spf is False
assert dkim is False
# Both pass
msg_both = EmailMessage()
msg_both["From"] = "alice@example.com"
msg_both["Authentication-Results"] = (
"mx.google.com; spf=pass smtp.mailfrom=example.com; dkim=pass header.d=example.com"
)
msg_both.set_content("test")
parsed = BytesParser(policy=policy.default).parsebytes(msg_both.as_bytes())
spf, dkim = EmailChannel._check_authentication_results(parsed)
assert spf is True
assert dkim is True
# SPF pass, DKIM fail
msg_spf_only = EmailMessage()
msg_spf_only["From"] = "alice@example.com"
msg_spf_only["Authentication-Results"] = (
"mx.google.com; spf=pass smtp.mailfrom=example.com; dkim=fail"
)
msg_spf_only.set_content("test")
parsed = BytesParser(policy=policy.default).parsebytes(msg_spf_only.as_bytes())
spf, dkim = EmailChannel._check_authentication_results(parsed)
assert spf is True
assert dkim is False
# DKIM pass, SPF fail
msg_dkim_only = EmailMessage()
msg_dkim_only["From"] = "alice@example.com"
msg_dkim_only["Authentication-Results"] = (
"mx.google.com; spf=fail smtp.mailfrom=example.com; dkim=pass header.d=example.com"
)
msg_dkim_only.set_content("test")
parsed = BytesParser(policy=policy.default).parsebytes(msg_dkim_only.as_bytes())
spf, dkim = EmailChannel._check_authentication_results(parsed)
assert spf is False
assert dkim is True
# ---------------------------------------------------------------------------
# Attachment extraction tests
# ---------------------------------------------------------------------------
def _make_raw_email_with_attachment(
from_addr: str = "alice@example.com",
subject: str = "With attachment",
body: str = "See attached.",
attachment_name: str = "doc.pdf",
attachment_content: bytes = b"%PDF-1.4 fake pdf content",
attachment_mime: str = "application/pdf",
auth_results: str | None = None,
) -> bytes:
msg = EmailMessage()
msg["From"] = from_addr
msg["To"] = "bot@example.com"
msg["Subject"] = subject
msg["Message-ID"] = "<m1@example.com>"
if auth_results:
msg["Authentication-Results"] = auth_results
msg.set_content(body)
maintype, subtype = attachment_mime.split("/", 1)
msg.add_attachment(
attachment_content,
maintype=maintype,
subtype=subtype,
filename=attachment_name,
)
return msg.as_bytes()
def test_fetch_new_messages_ignores_unauthorized_sender_before_attachments(monkeypatch) -> None:
raw = _make_raw_email_with_attachment(from_addr="blocked@example.com")
fake = _make_fake_imap(raw)
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
called = {"attachments": False}
def _extract_attachments(*_args, **_kwargs):
called["attachments"] = True
return []
monkeypatch.setattr(EmailChannel, "_extract_attachments", _extract_attachments)
cfg = _make_config(
allow_from=["allowed@example.com"],
allowed_attachment_types=["application/pdf"],
verify_dkim=False,
verify_spf=False,
)
channel = EmailChannel(cfg, MessageBus())
assert channel._fetch_new_messages() == ([], {"500"})
assert called["attachments"] is False
assert fake.store_calls == [(b"1", "+FLAGS", "\\Seen")]
def test_extract_attachments_saves_pdf(tmp_path, monkeypatch) -> None:
"""PDF attachment is saved to media dir and path returned in media list."""
monkeypatch.setattr("nanobot.channels.email.get_media_dir", lambda ch: tmp_path)
raw = _make_raw_email_with_attachment()
fake = _make_fake_imap(raw)
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
cfg = _make_config(allowed_attachment_types=["application/pdf"], verify_dkim=False, verify_spf=False)
channel = EmailChannel(cfg, MessageBus())
items, _ = channel._fetch_new_messages()
assert len(items) == 1
assert len(items[0]["media"]) == 1
saved_path = Path(items[0]["media"][0])
assert saved_path.exists()
assert saved_path.read_bytes() == b"%PDF-1.4 fake pdf content"
assert "500_doc.pdf" in saved_path.name
assert "[attachment:" in items[0]["content"]
def test_extract_attachments_disabled_by_default(monkeypatch) -> None:
"""With no allowed_attachment_types (default), no attachments are extracted."""
raw = _make_raw_email_with_attachment()
fake = _make_fake_imap(raw)
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
cfg = _make_config(verify_dkim=False, verify_spf=False)
assert cfg.allowed_attachment_types == []
channel = EmailChannel(cfg, MessageBus())
items, _ = channel._fetch_new_messages()
assert len(items) == 1
assert items[0]["media"] == []
assert "[attachment:" not in items[0]["content"]
def test_extract_attachments_mime_type_filter(tmp_path, monkeypatch) -> None:
"""Non-allowed MIME types are skipped."""
monkeypatch.setattr("nanobot.channels.email.get_media_dir", lambda ch: tmp_path)
raw = _make_raw_email_with_attachment(
attachment_name="image.png",
attachment_content=b"\x89PNG fake",
attachment_mime="image/png",
)
fake = _make_fake_imap(raw)
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
cfg = _make_config(
allowed_attachment_types=["application/pdf"],
verify_dkim=False,
verify_spf=False,
)
channel = EmailChannel(cfg, MessageBus())
items, _ = channel._fetch_new_messages()
assert len(items) == 1
assert items[0]["media"] == []
def test_extract_attachments_empty_allowed_types_rejects_all(tmp_path, monkeypatch) -> None:
"""Empty allowed_attachment_types means no types are accepted."""
monkeypatch.setattr("nanobot.channels.email.get_media_dir", lambda ch: tmp_path)
raw = _make_raw_email_with_attachment(
attachment_name="image.png",
attachment_content=b"\x89PNG fake",
attachment_mime="image/png",
)
fake = _make_fake_imap(raw)
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
cfg = _make_config(
allowed_attachment_types=[],
verify_dkim=False,
verify_spf=False,
)
channel = EmailChannel(cfg, MessageBus())
items, _ = channel._fetch_new_messages()
assert len(items) == 1
assert items[0]["media"] == []
def test_extract_attachments_wildcard_pattern(tmp_path, monkeypatch) -> None:
"""Glob patterns like 'image/*' match attachment MIME types."""
monkeypatch.setattr("nanobot.channels.email.get_media_dir", lambda ch: tmp_path)
raw = _make_raw_email_with_attachment(
attachment_name="photo.jpg",
attachment_content=b"\xff\xd8\xff fake jpeg",
attachment_mime="image/jpeg",
)
fake = _make_fake_imap(raw)
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
cfg = _make_config(
allowed_attachment_types=["image/*"],
verify_dkim=False,
verify_spf=False,
)
channel = EmailChannel(cfg, MessageBus())
items, _ = channel._fetch_new_messages()
assert len(items) == 1
assert len(items[0]["media"]) == 1
def test_extract_attachments_size_limit(tmp_path, monkeypatch) -> None:
"""Attachments exceeding max_attachment_size are skipped."""
monkeypatch.setattr("nanobot.channels.email.get_media_dir", lambda ch: tmp_path)
raw = _make_raw_email_with_attachment(
attachment_content=b"x" * 1000,
)
fake = _make_fake_imap(raw)
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
cfg = _make_config(
allowed_attachment_types=["*"],
max_attachment_size=500,
verify_dkim=False,
verify_spf=False,
)
channel = EmailChannel(cfg, MessageBus())
items, _ = channel._fetch_new_messages()
assert len(items) == 1
assert items[0]["media"] == []
def test_extract_attachments_max_count(tmp_path, monkeypatch) -> None:
"""Only max_attachments_per_email are saved."""
monkeypatch.setattr("nanobot.channels.email.get_media_dir", lambda ch: tmp_path)
# Build email with 3 attachments
msg = EmailMessage()
msg["From"] = "alice@example.com"
msg["To"] = "bot@example.com"
msg["Subject"] = "Many attachments"
msg["Message-ID"] = "<m1@example.com>"
msg.set_content("See attached.")
for i in range(3):
msg.add_attachment(
f"content {i}".encode(),
maintype="application",
subtype="pdf",
filename=f"doc{i}.pdf",
)
raw = msg.as_bytes()
fake = _make_fake_imap(raw)
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
cfg = _make_config(
allowed_attachment_types=["*"],
max_attachments_per_email=2,
verify_dkim=False,
verify_spf=False,
)
channel = EmailChannel(cfg, MessageBus())
items, _ = channel._fetch_new_messages()
assert len(items) == 1
assert len(items[0]["media"]) == 2
def test_extract_attachments_sanitizes_filename(tmp_path, monkeypatch) -> None:
"""Path traversal in filenames is neutralized."""
monkeypatch.setattr("nanobot.channels.email.get_media_dir", lambda ch: tmp_path)
raw = _make_raw_email_with_attachment(
attachment_name="../../../etc/passwd",
)
fake = _make_fake_imap(raw)
monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
cfg = _make_config(allowed_attachment_types=["*"], verify_dkim=False, verify_spf=False)
channel = EmailChannel(cfg, MessageBus())
items, _ = channel._fetch_new_messages()
assert len(items) == 1
assert len(items[0]["media"]) == 1
saved_path = Path(items[0]["media"][0])
# File must be inside the media dir, not escaped via path traversal
assert saved_path.parent == tmp_path
# ---------------------------------------------------------------------------
# Agent-initiated file attachment tests (send with media)
# ---------------------------------------------------------------------------
@pytest.mark.asyncio
async def test_send_with_single_file_attachment(tmp_path, monkeypatch) -> None:
"""Agent sends an email with a single file attached."""
sent_messages: list[EmailMessage] = []
class FakeSMTP:
def __init__(self, _host: str, _port: int, timeout: int = 30) -> None:
self.timeout = timeout
def __enter__(self):
return self
def __exit__(self, exc_type, exc, tb):
return False
def starttls(self, context=None):
return None
def login(self, _user: str, _pw: str):
return None
def send_message(self, msg: EmailMessage):
sent_messages.append(msg)
monkeypatch.setattr("nanobot.channels.email.smtplib.SMTP", lambda h, p, timeout=30: FakeSMTP(h, p, timeout=timeout))
# Create a real temp file to attach
attachment = tmp_path / "report.pdf"
attachment.write_bytes(b"%PDF-1.4 fake pdf content")
channel = EmailChannel(_make_config(), MessageBus())
await channel.send(
OutboundMessage(
channel="email",
chat_id="alice@example.com",
content="Please find the report attached.",
media=[str(attachment)],
)
)
assert len(sent_messages) == 1
sent = sent_messages[0]
assert sent["To"] == "alice@example.com"
assert sent.is_multipart(), "Email with attachment should be multipart"
# Walk parts to find the attachment
attachment_parts = []
for part in sent.walk():
if part.get_content_disposition() == "attachment":
attachment_parts.append(part)
assert len(attachment_parts) == 1
att = attachment_parts[0]
assert att.get_filename() == "report.pdf"
assert att.get_content_type() == "application/pdf"
assert att.get_payload(decode=True) == b"%PDF-1.4 fake pdf content"
@pytest.mark.asyncio
async def test_send_with_multiple_file_attachments(tmp_path, monkeypatch) -> None:
"""Agent sends an email with multiple files attached."""
sent_messages: list[EmailMessage] = []
class FakeSMTP:
def __init__(self, _host: str, _port: int, timeout: int = 30) -> None:
self.timeout = timeout
def __enter__(self):
return self
def __exit__(self, exc_type, exc, tb):
return False
def starttls(self, context=None):
return None
def login(self, _user: str, _pw: str):
return None
def send_message(self, msg: EmailMessage):
sent_messages.append(msg)
monkeypatch.setattr("nanobot.channels.email.smtplib.SMTP", lambda h, p, timeout=30: FakeSMTP(h, p, timeout=timeout))
file1 = tmp_path / "doc.pdf"
file1.write_bytes(b"%PDF-1.4 doc")
file2 = tmp_path / "image.png"
file2.write_bytes(b"\x89PNG fake image")
file3 = tmp_path / "notes.txt"
file3.write_bytes(b"Hello, this is a text note.")
channel = EmailChannel(_make_config(), MessageBus())
await channel.send(
OutboundMessage(
channel="email",
chat_id="bob@example.com",
content="Multiple files attached.",
media=[str(file1), str(file2), str(file3)],
)
)
assert len(sent_messages) == 1
sent = sent_messages[0]
assert sent.is_multipart()
attachment_parts = []
for part in sent.walk():
if part.get_content_disposition() == "attachment":
attachment_parts.append(part)
assert len(attachment_parts) == 3
filenames = {p.get_filename() for p in attachment_parts}
assert filenames == {"doc.pdf", "image.png", "notes.txt"}
@pytest.mark.asyncio
async def test_send_skips_missing_attachment_file(tmp_path, monkeypatch) -> None:
"""Non-existent attachment file is skipped without breaking the send."""
sent_messages: list[EmailMessage] = []
class FakeSMTP:
def __init__(self, _host: str, _port: int, timeout: int = 30) -> None:
self.timeout = timeout
def __enter__(self):
return self
def __exit__(self, exc_type, exc, tb):
return False
def starttls(self, context=None):
return None
def login(self, _user: str, _pw: str):
return None
def send_message(self, msg: EmailMessage):
sent_messages.append(msg)
monkeypatch.setattr("nanobot.channels.email.smtplib.SMTP", lambda h, p, timeout=30: FakeSMTP(h, p, timeout=timeout))
existing = tmp_path / "real.txt"
existing.write_text("I exist")
channel = EmailChannel(_make_config(), MessageBus())
await channel.send(
OutboundMessage(
channel="email",
chat_id="alice@example.com",
content="One attachment is missing.",
media=[
str(existing),
str(tmp_path / "nonexistent.pdf"),
],
)
)
assert len(sent_messages) == 1
sent = sent_messages[0]
assert sent.is_multipart()
attachment_parts = []
for part in sent.walk():
if part.get_content_disposition() == "attachment":
attachment_parts.append(part)
# Only the existing file should be attached
assert len(attachment_parts) == 1
assert attachment_parts[0].get_filename() == "real.txt"
body = sent.get_body(preferencelist=("plain",))
assert body is not None
assert "[attachment: nonexistent.pdf - send failed]" in body.get_content()
@pytest.mark.asyncio
async def test_send_skips_oversized_attachment_file(tmp_path, monkeypatch) -> None:
"""Attachment exceeding max_attachment_size is skipped with a visible note."""
sent_messages: list[EmailMessage] = []
class FakeSMTP:
def __init__(self, _host: str, _port: int, timeout: int = 30) -> None:
self.timeout = timeout
def __enter__(self):
return self
def __exit__(self, exc_type, exc, tb):
return False
def starttls(self, context=None):
return None
def login(self, _user: str, _pw: str):
return None
def send_message(self, msg: EmailMessage):
sent_messages.append(msg)
monkeypatch.setattr("nanobot.channels.email.smtplib.SMTP", lambda h, p, timeout=30: FakeSMTP(h, p, timeout=timeout))
attachment = tmp_path / "too-large.bin"
attachment.write_bytes(b"1234")
channel = EmailChannel(_make_config(max_attachment_size=3), MessageBus())
await channel.send(
OutboundMessage(
channel="email",
chat_id="alice@example.com",
content="Attachment should be skipped.",
media=[str(attachment)],
)
)
assert len(sent_messages) == 1
sent = sent_messages[0]
assert not sent.is_multipart()
assert "[attachment: too-large.bin - too large]" in sent.get_content()
@pytest.mark.asyncio
async def test_send_limits_outbound_attachment_count(tmp_path, monkeypatch) -> None:
"""Only max_attachments_per_email outbound attachments are included."""
sent_messages: list[EmailMessage] = []
class FakeSMTP:
def __init__(self, _host: str, _port: int, timeout: int = 30) -> None:
self.timeout = timeout
def __enter__(self):
return self
def __exit__(self, exc_type, exc, tb):
return False
def starttls(self, context=None):
return None
def login(self, _user: str, _pw: str):
return None
def send_message(self, msg: EmailMessage):
sent_messages.append(msg)
monkeypatch.setattr("nanobot.channels.email.smtplib.SMTP", lambda h, p, timeout=30: FakeSMTP(h, p, timeout=timeout))
file1 = tmp_path / "first.txt"
file1.write_text("first")
file2 = tmp_path / "second.txt"
file2.write_text("second")
channel = EmailChannel(_make_config(max_attachments_per_email=1), MessageBus())
await channel.send(
OutboundMessage(
channel="email",
chat_id="alice@example.com",
content="Only one attachment should be sent.",
media=[str(file1), str(file2)],
)
)
assert len(sent_messages) == 1
sent = sent_messages[0]
attachment_parts = []
for part in sent.walk():
if part.get_content_disposition() == "attachment":
attachment_parts.append(part)
assert len(attachment_parts) == 1
assert attachment_parts[0].get_filename() == "first.txt"
body = sent.get_body(preferencelist=("plain",))
assert body is not None
assert "[attachment: second.txt - too many attachments]" in body.get_content()
@pytest.mark.asyncio
async def test_send_with_unknown_mime_type_attachment(tmp_path, monkeypatch) -> None:
"""File with unknown extension gets application/octet-stream MIME type."""
sent_messages: list[EmailMessage] = []
class FakeSMTP:
def __init__(self, _host: str, _port: int, timeout: int = 30) -> None:
self.timeout = timeout
def __enter__(self):
return self
def __exit__(self, exc_type, exc, tb):
return False
def starttls(self, context=None):
return None
def login(self, _user: str, _pw: str):
return None
def send_message(self, msg: EmailMessage):
sent_messages.append(msg)
monkeypatch.setattr("nanobot.channels.email.smtplib.SMTP", lambda h, p, timeout=30: FakeSMTP(h, p, timeout=timeout))
attachment = tmp_path / "data.unknown_ext_xyz"
attachment.write_bytes(b"some binary data")
channel = EmailChannel(_make_config(), MessageBus())
await channel.send(
OutboundMessage(
channel="email",
chat_id="alice@example.com",
content="Unknown MIME type.",
media=[str(attachment)],
)
)
assert len(sent_messages) == 1
sent = sent_messages[0]
assert sent.is_multipart()
attachment_parts = []
for part in sent.walk():
if part.get_content_disposition() == "attachment":
attachment_parts.append(part)
assert len(attachment_parts) == 1
att = attachment_parts[0]
assert att.get_content_type() == "application/octet-stream"
assert att.get_filename() == "data.unknown_ext_xyz"
@pytest.mark.asyncio
async def test_send_with_media_and_reply_subject_and_in_reply_to(tmp_path, monkeypatch) -> None:
"""Attachments work together with reply subject and In-Reply-To headers."""
sent_messages: list[EmailMessage] = []
class FakeSMTP:
def __init__(self, _host: str, _port: int, timeout: int = 30) -> None:
self.timeout = timeout
def __enter__(self):
return self
def __exit__(self, exc_type, exc, tb):
return False
def starttls(self, context=None):
return None
def login(self, _user: str, _pw: str):
return None
def send_message(self, msg: EmailMessage):
sent_messages.append(msg)
monkeypatch.setattr("nanobot.channels.email.smtplib.SMTP", lambda h, p, timeout=30: FakeSMTP(h, p, timeout=timeout))
attachment = tmp_path / "summary.pdf"
attachment.write_bytes(b"%PDF-1.4 summary")
channel = EmailChannel(_make_config(), MessageBus())
channel._last_subject_by_chat["alice@example.com"] = "Original subject"
channel._last_message_id_by_chat["alice@example.com"] = "<orig@example.com>"
await channel.send(
OutboundMessage(
channel="email",
chat_id="alice@example.com",
content="Reply with attachment.",
media=[str(attachment)],
)
)
assert len(sent_messages) == 1
sent = sent_messages[0]
assert sent["Subject"] == "Re: Original subject"
assert sent["In-Reply-To"] == "<orig@example.com>"
assert sent["References"] == "<orig@example.com>"
attachment_parts = []
for part in sent.walk():
if part.get_content_disposition() == "attachment":
attachment_parts.append(part)
assert len(attachment_parts) == 1
assert attachment_parts[0].get_filename() == "summary.pdf"